(E)-3-(1,3-benzodioxol-5-yl)-1-[7-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-5-(4-methoxyphenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-6-yl]prop-2-en-1-one | 1400767-20-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-3-(1,3-benzodioxol-5-yl)-1-[7-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-5-(4-methoxyphenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-6-yl]prop-2-en-1-one
• 英文别名: (E)-3-(1,3-benzodioxol-5-yl)-1-[7-[(E)-2-(1,3-benzodioxol-5-yl)ethenyl]-5-(4-methoxyphenyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-6-yl]prop-2-en-1-one
• CAS: 1400767-20-5
• 化学式: C₃₃H₂₆N₂O₆S
• 分子量: 578.645
• InChiKey: QWWNBWVIWCWNOI-HMMKTVFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  胡椒醛 、 3-溴丙炔 、 5-acetyl-4-(4-methoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 以65%的产率得到(E)-3-(1,3-benzodioxol-5-yl)-1-[7-[(E)-2-(1,3-benzodioxol-5-yl)vinyl]-5-(4-methoxyphenyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-6-yl]prop-2-en-1-one
  参考文献：
  名称：

  One pot efficient diversity oriented synthesis of polyfunctional styryl thiazolopyrimidines and their bio-evaluation as antimalarial and anti-HIV agents

  摘要：

  An efficient one pot synthesis of a series of pluripotent (E)-1-(3-methyl-5-aryl-7-styryl-5H-thiazolo[3,2-a]pyrimidin-6-yl)-3-arylprop-2-en-1-ones is reported. It involves reaction of 5-acetyl-6-methyl-4-aryldihydropyrimidine-2-thiones, propargyl bromide and aromatic aldehydes in presence of ethanolic KOH. The newly synthesized compounds were evaluated for antimalarial activity against Plasmodium falciparum and as HIV-RT inhibitors. Most of the compound displayed potent antimalarial activity with IC50 < 2 mu g/mL Compounds 6, 11 and 20 showed better activity against P. falciparum K1 strains in comparison to standard drug chloroquine. Compounds 6, 11, and 16 exhibited 73.44, 66.92, and 70.81% HIV-RT inhibition at 100 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.018

文献信息

• One pot efficient diversity oriented synthesis of polyfunctional styryl thiazolopyrimidines and their bio-evaluation as antimalarial and anti-HIV agents
  作者：Seerat Fatima、Anindra Sharma、Reshu Saxena、Rajkamal Tripathi、Sanjeev K. Shukla、Swaroop Kumar Pandey、Renu Tripathi、Rama P. Tripathi

  DOI：10.1016/j.ejmech.2012.07.018

  日期：2012.9

  An efficient one pot synthesis of a series of pluripotent (E)-1-(3-methyl-5-aryl-7-styryl-5H-thiazolo[3,2-a]pyrimidin-6-yl)-3-arylprop-2-en-1-ones is reported. It involves reaction of 5-acetyl-6-methyl-4-aryldihydropyrimidine-2-thiones, propargyl bromide and aromatic aldehydes in presence of ethanolic KOH. The newly synthesized compounds were evaluated for antimalarial activity against Plasmodium falciparum and as HIV-RT inhibitors. Most of the compound displayed potent antimalarial activity with IC50 < 2 mu g/mL Compounds 6, 11 and 20 showed better activity against P. falciparum K1 strains in comparison to standard drug chloroquine. Compounds 6, 11, and 16 exhibited 73.44, 66.92, and 70.81% HIV-RT inhibition at 100 mu g/mL. (C) 2012 Elsevier Masson SAS. All rights reserved.